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With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h;
General procedure: CuI (0.05 equiv), 1,10-phenanthroline (0.1 equiv) and K2CO3 (2 equiv) were placed in an oven-dried screw-capped test tube with Teflon-lined septum that was filled with nitrogen. About 2.5 mL of dry DMF was then added at room temperature. Now the corresponding aryl iodide (1.0 mmol) was added followed by MBI or FMBI (1.0 equiv) and the tube was placed in the preheated oil bath at 140 C and the reaction mixture was magnetically stirred for 22 h. After complete disappearance of iodobenzene (the progress of the reaction was followed by TLC), the reaction mixture was allowed to cool to room temperature. Then water was added and the reaction mixture was extracted with ethyl acetate. After removal of the solvent in vacuum, the crude residue was purified by column chromatography.5- (or 6-) (Difluoromethoxy)-2-(phenylsulfanyl)-1H-benzimidazole (1).
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 120℃; for 10h;Inert atmosphere; Sealed tube;
To the tube was added 1,4-diiodobenzene (2 g, 6.06 mmol)Morpholine-3-one (700 mg, 6.92 mmol), potassium carbonate (2.5 g, 18.1 mmol), cuprous iodide (230 mg, 1.21 mmol), N1, N2-dimethylethylenediamine(110 [mu] L, 1.21 mmol) and dimethylsulfoxide (6 mL). The mixture was heated to 120 C and stirred for 10 hours under a nitrogen atmosphere. The mixture was cooled to room temperature, quenched by addition of water (20 mL), extracted with dichloromethane (15 mL x 3) and dried over anhydrous sodium sulfate. The crude product was purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 1/5) to give a white solid (1.22 g, 66.4%).
tert-butyl 3-(4-iodobenzoyl)azetidine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
7.2%
A three-necked flask was charged with 1,4-diiodobenzene (0.41 g) and diethyl ether (11 mL). The flask was evacuated and backfilled with nitrogen gas. To the solution was added n-BuLi (0.46 mL, 2.65 mol/L solution in n-hexane) dropwise at -78 C and the reaction mixture was stirred for 1 hour at the same temperature. The solution of tert-butyl 3-[methoxy(methyl)carbamoyl]azetidine-l-carboxylate (0.30 g) in diethyl ether (1.5 mL) was added dropwise to the mixture at -78 C and the reaction was stirred for 2 hours. The reaction was allowed to warm to room temperature and stirred for 30 minutes. After cooling to 0 C, the reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified with OH-type silica gel column chromatography (10"60% EtOAc in /hexane) to give the title compound (34 mg, 7.2% yield) as yellow oil. MS (ESI) m/z 410 [M+l]. RT = 1.230 min. LCMS condition B.
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